Touby Prize

How a former desperate freelancer became a networking millionaire.

The media in-crowd always had a hard time taking freelance writer turned networking entrepreneur Laurel Touby all that seriously, which is why there was so much surprise over the news last week that she’d sold her MediaBistro.com (such a goofy name!) to Jupitermedia for $23 million. The animus in the blogosphere was aimed squarely at Touby (Her?! The party gal with the feather boa?!), but you could tell it really all boiled down to self-loathing. As in, What the hell is wrong with me? Why haven’t I figured out how to sell out like that? Wasn’t this sort of instant wealth from a half-baked idea thing supposed to have ended with the dot-com bubble?

Such is the hierarchy of Internet-millionaire envy: We can begrudgingly accept the success of obvious geniuses (Sergey Brin, Larry Page) who at least had the common courtesy to establish their geek bona fides by studying computer science at Stanford. We can kind of accept the insta-wealth of enterprising dorks (Steve Chen, Chad Hurley) who, while not necessarily geniuses, launched exactly the right thing at the right time. But when a smiley, 44-year-old former desperate magazine freelancer, who started her company way back in 1993 by throwing anti-loneliness cocktail parties for fellow desperate freelancers, personally scores a $12 million payday (she owns 60 percent of MediaBistro), well, what the hell?

Turns out Touby was, no kidding, a secret business genius. She cornered the market on media-job listings and generated a Learning Annex–esque set of classes with all the can-do sense of possibility contained in women’s magazine cover lines (“Writing Travel Guidebooks: Live the Dream: Travel, Write and Get Paid,” “Career Reinvention Toolkit,” “How to Write Chick Lit”). Meanwhile, Touby was collecting lots and lots of cash from the out-crowd: thousands across the country, in media markets large and small, who pay $49 per year for an annual MediaBistro membership and a piece of the dream.

The fact that MediaBistro happens to have a prominent Website (with a number of high-profile blogs, including TVnewser) made it seem like Touby, of all people, got to benefit from the current new-media bubble. In fact, she’d created, over the course of fourteen grinding years, a rather substantial company with multiple, steady revenue streams.

Still, that didn’t stop Gawker from concluding that “it is 1997” again. In fact, Touby’s success underscores the difference between the current (seeming) bubble and that of the late nineties: The way to cash out now is to get bought out, not to go public. And until the right buyer shows up, all that most of us can do is stand back and guesstimate what’s worth what. Touby’s company isn’t at all sexy, so just about everybody underestimated it.